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20 Longmeadow Drive, Westwood
$4,495,000
6 Beds ⋅ 7 Baths ⋅ 73535655 MLS
Your family's everything dream home is already built for you with both elegance and warmth as soon as you step in. Light-filled rooms throughout, featuring window seating both in the kitchen's separate eating area and in the hexagonal library. Floor to vaulted ceiling windows that flank the grand stone and brick fireplace in the Great Room and carry you to the gourmet kitchen with quartz countertop island for fabulous entertaining. This leads through a fully equipped butler's pantry to an unmatched dining room with built-in cabinetry, fireplace, and arched windows. Flooring of marble, tile and oak are found throughout, with views front to back. Or choose the magnificent sunroom, which steps out to stone patios for gatherings all across the yard with a level grassy area for endless possibilities. Walk the sidewalks with stately Boston street lamps. Fall asleep at night in luxury with a fireplace, spa bath ensuite, and choose your outfits in the morning from your two walk-in closets.

20 Longmeadow Drive, Westwood

Listing courtesy of Listing Agent: Peter Cwieka from Listing Office: Media Realty Group Inc..

157 Grove Street, Westwood
$4,000,000
5 Beds ⋅ 4 Baths ⋅ 73542491 MLS
A private estate spanning 11 spectacular acres, this distinguished 1912 residence offers timeless character and exceptional privacy in one of the Boston area's most coveted settings. The five-BR home features 4,500+ square feet of beautifully maintained living space blending classic architectural details with modern comfort. Grand living and dining rooms, a sun-drenched conservatory, and an intimate library create a sophisticated backdrop for entertaining. Center island chef's kitchen and FP'd family room. Period details include custom millwork, French doors, a spacious butler’s pantry and multiple fireplaces. Expansive porches and patios overlook lush gardens and sweeping grounds, leading to a tucked-away pool. An oversized 3-car carriage house with loft adds further versatility. This rare offering includes a separate buildable lot, providing an opportunity for expansion or legacy compound. Minutes to the commuter rail, major routes, and premier shopping. An irreplaceable opportunity.

157 Grove Street, Westwood

Listing courtesy of Listing Agent: Bell Property Partners from Listing Office: Compass.

272 Fox Hill St, Westwood
$3,600,000
7 Beds ⋅ 5 Baths ⋅ 73573909 MLS
Built in 1850, this residence is a classic example of mid-19th-century New England architecture. Set on 8.93 potentially subdividable acres on Westwood's iconic Fox Hill Street, it is rich in historic character. It offers 4,241sf of living area and features hardwood floors, generously sized windows, multiple fireplaces, and built-in cabinetry. The entry foyer opens to a music room, living room, dining room and library, each offering distinctive character and period details. The kitchen includes granite counters, double wall ovens, an eat-in dining area and large windows. A butler’s pantry with extensive storage, exterior access and an adjoining laundry room adds everyday functionality. Two first-floor bedrooms or offices and a full bath provide versatility for guests, work or additional living space. Upstairs, just off the landing, is an en-suite primary bedroom, a second en-suite bedroom and three additional bedrooms served by a separate hall bath. Outside, the covered porch, the deck, and a large antique barn overlook beautiful rolling lawns and woods that abut over 300 acres of conservation land with miles of walking trails.

272 Fox Hill St, Westwood

Listing courtesy of Listing Agent: John Boyle from Listing Office: LandVest, Inc..

54 Meadowbrook Road, Westwood
$2,295,000
4 Beds ⋅ 5 Baths ⋅ 73559295 MLS
Prime location on culdesac - Two year young custom built contemporary style home with thoughtful detail and design boasts all you would expect with high ceilings, white oak floors, oversize windows, spacious bright rooms and comfortable living space. Welcome your guests onto the wide front porch and into the large open entry foyer. There is a front sitting room, office space and separate expansive dining room offering streams of natural light. The generously sized chefs style kitchen features SubZero and Wolf appliances, two islands and separate breakfast area. Open from the kitchen is the family room with fireplace, vaulted ceiling and access to the wrap around back deck overlooking the large level yard. The first floor guest suite offers a multigenerational living option. The second floor hosts the primary suite with deep walk in closet, radiant floors, double sinks and luxurious tub and separate shower, laundry room and the additional bedrooms with bath. Walkout lower level boasts a gym area, game room, full bath, theatre, and plumbed for bar. Sizable mudroom has plenty of additional storage space and access to the three car garage. Oversize patio is ideal for outdoor dining or enjoy the basketball, sports court. Prime commuting access, close to shops, train, major routes, restaurants. Pine Hill school and quiet culdesac setting makes this the perfect find.

54 Meadowbrook Road, Westwood

Listing courtesy of Listing Agent: Elena Price from Listing Office: Coldwell Banker Realty - Westwood.

25 Clearwater Dr, Westwood
$1,599,000
4 Beds ⋅ 4 Baths ⋅ 73569091 MLS
From the moment you enter, the generous proportions and inviting character of this beautifully updated Cape set it apart. Meticulously maintained and offering over 3,200 square feet of above-grade living and over 1300 below grade, the home features exceptionally large rooms throughout and the rare flexibility of primary suites on both levels, creating a home that feels substantial yet warm and welcoming.The renovated kitchen features sought-after white cabinetry, quartz countertops, and a contrasting blue center island, opening directly into the expansive family room. A soaring vaulted ceiling and dramatic floor-to-ceiling brick fireplace create an impressive focal point, while hardwood floors bring warmth and character throughout. Just off the family room, the newer four-season room is one of the home's most special features. Surrounded by windows and filled with natural light, it's a beautiful retreat overlooking the private backyard.The main level continues with a large living room enhanced by beautiful molding, a spacious dining room, half bath, and an impressive first-floor primary suite. A spectacular custom walk-in closet provides exceptional storage and organization, while the beautifully renovated en-suite bath features a sophisticated design and an impressive walk-in shower with a polished, spa-like feel.Upstairs are three generously sized bedrooms, including a second primary suite with its own private bath, along with an additional full bathroom. This versatile layout works beautifully for family, guests, or multigenerational living while still providing plenty of privacy.The finished lower level adds even more versatility for recreation, a home gym, office, hobbies, or additional living area.Set on a large, private lot with a two-car garage, 25 Clearwater Drive brings together beautifully updated interiors, impressive room sizes, architectural character, and a remarkably flexible floor plan. Refined yet wonderfully comfortable, this is a home where quality, character, and thoughtful updates come together beautifully.

25 Clearwater Dr, Westwood

Listing courtesy of Listing Agent: Lori Seavey Realty Team from Listing Office: Keller Williams Elite.

138 Forbes Rd, Westwood
$1,299,000
4 Beds ⋅ 3 Baths ⋅ 73585576 MLS
Welcome to this classic 4-bedroom, 2.5-bath Colonial offering timeless charm and inviting spaces throughout. The spacious kitchen features a unique half-round dining addition with a wall of windows and built-in window seating overlooking the in-ground pool and beautifully manicured grounds—perfect for everyday dining or entertaining. The fireplaced family room is enhanced by custom millwork, while the formal living and dining rooms feature picture and bay windows that fill the spaces with natural light. A bright sunroom with a Palladian window and double sliders creates a seamless connection to the outdoors. Upstairs, four comfortable bedrooms include a private primary en-suite. Additional highlights include beautiful hardwood floors, natural gas heat, two-car garage and a desirable location near Downey Elementary - A Massachusetts School of Recognition. Nestled in an established neighborhood, this home is just moments from the shops and amenities of University Avenue, with easy commuter access to Route 95.

138 Forbes Rd, Westwood

Listing courtesy of Listing Agent: William Concannon from Listing Office: Louise Condon Realty.

175 Colburn Street, Westwood
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 73572685 MLS
Welcome to 175 Colburn Street, a move-in-ready Colonial nestled in Westwood’s coveted Maze neighborhood, offering a wonderful combination of space, privacy, and convenience. Built in 2015, this thoughtfully designed 4-bedroom home features an inviting open-concept first floor with a spacious living room, dining room, and kitchen complete with granite countertop, island and breakfast nook that has sliders leading to outside deck. Upstairs, generously sized bedrooms include a private primary suite with walk-in closet and conveniently located 2nd floor laundry room.A standout feature of this home is its beautifully private backyard, bordered by mature woods, creating a peaceful setting. The home also offers exceptionally generous ceiling height throughout, including the full unfinished basement, which presents exciting potential for future finished living space, a recreation room, home gym, office, or additional storage. With a walkout directly to the backyard, the lower level offers both flexibility and excellent expansion potential. Conveniently located near Westwood’s schools, commuter routes, shopping, dining, and local amenities, 175 Colburn Street is a special opportunity to enjoy the space and feel of a newer Colonial in one of Westwood’s most desirable neighborhoods.

175 Colburn Street, Westwood

Listing courtesy of Listing Agent: Yebba Roy Team from Listing Office: Coldwell Banker Realty - Westwood.

444 Clapboardtree Street, Westwood
$1,275,000
4 Beds ⋅ 3 Baths ⋅ 73580898 MLS
New Price ! Opportunity to own a rare piece of level land set back on almost 2 private tree lined acres. The existing home offers substantial space for a family with the opportunity to move in and enjoy as is or update, renovate, or expand according to your vision. The home has been improved over the years and features multiple levels of living space, including a cherry eat-in kitchen with center island, dining room, and family room with fireplace. Above the family room is an additional bedroom and office with a full bath. The second floor offers three additional bedrooms and another full bath. A semi-finished enclosed garage provides valuable additional space, including laundry and a bathroom, with convenient access to both the backyard and lower level. The private backyard is a true highlight, featuring an inground pool, pool house, and shed, creating a wonderful setting for summer entertaining, recreation, and enjoying the surrounding natural setting. For those looking to personalize the property, there is plenty of opportunity to bring the existing home into today's standards, expand the living space, or pursue a larger-scale renovation or future redevelopment, subject to applicable approvals. The combination of an existing home, substantial acreage, privacy, and flexibility makes this a particularly unique property.The home is being sold **as-is**. A new heating system has been installed. Chimney requires repair. Buyer will need to hook up to public sewer at the street.**Please do not walk the property without the listing agent.**--

444 Clapboardtree Street, Westwood

Listing courtesy of Listing Agent: Elena Price from Listing Office: Coldwell Banker Realty - Westwood.

355 High St, Westwood
$1,050,000
5 Beds ⋅ 3 Baths ⋅ 73558725 MLS
NEW PRICE! Exceptional opportunity to live in Westwood on a two-acre property which offers the perfect balance of privacy and convenience, easy access to the town center, major commuter routes in premier MetroWest community. Built in 1929, this classic Colonial showcases timeless architectural character, featuring high ceilings, oversized windows and french doors providing an abundance of natural light, and hardwood floors throughout. Rich in charm and original detail, this home presents a rare opportunity to restore and reimagine a property with enduring appeal. The expansive grounds are a true highlight—an exceptional, rolling yard surrounded by a serene, natural setting that offers both tranquility and space for outdoor living, entertaining, or future enhancements. Located in highly sought-after Westwood—known for its top-rated schools, strong community feel —this property represents a unique opportunity for buyers looking to customize and create their ideal home in a prime location. No open houses.

355 High St, Westwood

Listing courtesy of Listing Agent: Jane Wemyss from Listing Office: Compass.

1036 High St, Westwood
$849,000
3 Beds ⋅ 2 Baths ⋅ 73581627 MLS
Situated along a quiet stretch of Route 109, this Colonial style residence occupies a prime Westwood location, providing convenient access to Westwood center, local schools, major routes, and nearby natural attractions like the Sen Ki Trail and Buckmaster Pond. Offering hardwood flooring and abundant storage throughout the home, the flexible layout presents outstanding potential for customization. The main level opens into a spacious living room centered around a classic brick fireplace, with French doors leading into the adjoining dining room. Sliding glass doors extend to a substantial screened porch that overlooks the wooded backyard and garden divided by a white picket fence. The kitchen features a dedicated pantry closet and direct exterior access, while a full bathroom and two additional multipurpose rooms provide flexibility for a bedroom, home office, den, playroom, or whatever best suits your needs. The upper level comprises a primary suite alongside two additional bedrooms, all served by a well-proportioned full hallway bathroom. A walk-in attic offers extensive storage capacity and opportunities for future adaptation. The basement provides direct access to the garage, as well as a dedicated laundry space and a workshop with high ceilings. The level lawn in the back yard provides ample outdoor space for activities and a serene setting for leisure time. Notable mechanical and structural features include central air conditioning, a recently replaced roof, and an updated hot water heater. This property presents an exceptional opportunity to implement custom improvements while benefiting from an advantageous location, adaptable living spaces, and a distinctive natural environment. See the possibilities now in the virtual tour.

1036 High St, Westwood

Listing courtesy of Listing Agent: The Jowdy Group from Listing Office: RE/MAX Distinct Advantage.

64 Pheasant Hill Street, Westwood
$849,000
4 Beds ⋅ 2 Baths ⋅ 73578090 MLS
Quintessential New England Cape set on an exceptional 12,235± SF lot and located in a popular side street neighborhood on the flat of the hill. Updates include bathrooms, interior painting, roof, windows, heating system, a/c mini splits, hot water heater, 200 Amp electrical panel, stainless steel chimney liner, bulkhead & fencing. Bright, sunny east facing living room with fireplace & build-in shelves opens into a spacious formal dining room with built-in corner cupboard offering access to the expansive back yard & one-car attached garage. A cozy kitchen, updated hall bathroom, bedroom/office and den complete the first floor. The second floor features three air conditioned bedrooms and an updated hall bathroom with skylight. The unfinished basement with kids playroom offers ample storage space. Exterior living space is enhanced by a rear deck and side covered porch. Enjoy convenient access to neighborhood Pheasant Hill Park & adjacent walking trails, Hale Reservation, Westwood Center, Sheehan Elementary School, High School & Middle School. If you are looking for a friendly neighborhood with residents from all walks of life, pet lovers, walkers, gardeners, nature lovers & more, the Pheasant Hill neighborhood, with it's own neighborhood social media page, is a great choice.

64 Pheasant Hill Street, Westwood

Listing courtesy of Listing Agent: Tom Aaron from Listing Office: Coldwell Banker Realty - Wellesley.

120 University Ave Unit 2308, Westwood
$759,000
2 Beds ⋅ 2 Baths ⋅ 73550537 MLS ⋅ ['Westwood Place'] BLDG.
Newly luxury condo ready for move in! This 2B2B unit is the best in the building and comes with a garage parking spot! Covered by hardwood floors, the unit is 1320 sq ft with everything you need! Enjoy numerous upgrades installed during construction. There is an open living space with a granite countertop kitchen that has its own island, stainless steel appliances, a large fridge and gas range. A private balcony is attached to the central space. Both bedrooms are spacious and comfortable. Inside the master there are two large walk-in closets. SUPERB LOCATION! Walking distance to AMTRAK & MBTA lines means going to Boston takes less than 20 min! 2 min walk to Westwood Mall has everything you need from Wegmans, Target, Nordstrom Rack, HomeGoods, restaurants, coffee shops, gyms and much more! Easy access to R95 & R93 also means driving anywhere is a breeze.

120 University Ave Unit 2308, Westwood

Listing courtesy of Listing Agent: The Ridick Revis Group from Listing Office: Compass.

21 Webster Street, Westwood
$749,000
3 Beds ⋅ 2 Baths ⋅ 73590640 MLS
Available for the first time in 73 years! Embrace the opportunity to restore, renovate or expand this classic hip roof Colonial originally built in 1953 as the "sales model home" for the neighborhood by the distinguished Alfred Magaletta Construction Company. This well constructed 1,834± SF home with unlimited potential is set on a lovely 8,033± SF lot in a prized neighborhood side street just minutes to the reimagined Village of Islington. Bright, east facing entry hall & living room with bay window & fireplace opens into a spacious formal dining room with built-in corner cabinet plus a nostalgic 1950's kitchen, half bath & den with direct access to a one-car attached garage complete the first floor. The second floor offers three spacious bedrooms with sparkling hardwood floors and a full bathroom. The basement features a cozy wood paneled recreation room with bar, shelving and ample unfinished storage. Enjoy easy access to I-95, Islington Village shops & restaurants, new Pine Hill Elementary School, Roche Bros supermarket, CVS pharmacy, Morrison Park, School Street Playground, Forest Hills bus line, Islington Train Station, Legacy Place, University Station and much more.

21 Webster Street, Westwood

Listing courtesy of Listing Agent: Tom Aaron from Listing Office: Coldwell Banker Realty - Wellesley.

355 Canton St, Westwood
$600,000
3 Beds ⋅ 3 Baths ⋅ 73442807 MLS
Excellent opportunity for investors, developers or buyers looking to restore and customize a home, or raze it and build new! Great location in Westwood on a corner lot. Sold as-is. Cash sale preferred. Spacious ranch. Living room with fireplace & hardwood floors. Family room with fireplace off the back of the house overlooking the enclosed in-ground pool. 3 bedrooms. Full bath with access to the primary bedroom and hallway. The basement has lots of potential for additional living space. Had been finished at one point in time. Basement has water damage and mold from a burst hot water tank. 3rd fireplace is in the basement. Multiple Offers! Offer deadline is Thursday, October 16th at 2:00 PM. This does not preclude the seller from accepting an offer earlier.

355 Canton St, Westwood

Listing courtesy of Listing Agent: Watson Homes Team from Listing Office: RE/MAX Real Estate Center.

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